反应详情

70 ml of tetrahydrofuran was added to 25.3 g (1.04 mol) of magnesium, and a solution having 9.45 g (0.087 mol) of ethyl bromide and 200 g (0.867 mol) of (R)-2-phenyl-1-(4-chlorophenyl)propane dissolved in 250 ml of tetrahydrofuran was dropwise added thereto over a period of 30 minutes at room temperature with stirring, followed by stirring for 6 hours under reflux. After the mixture was cooled to room temperature, 650 ml of tetrahydrofuran was added thereto. The above reaction liquid was dropwise added to a solution having 112 g (0.44 mol) of trimethoxyboron dissolved in 300 ml of tetrahydrofuran over a period of 1 hour at −20° C., followed by stirring for 1 hour. The temperature was raised to 0° C., 700 ml of 3M hydrochloric acid was dropwise added, followed by stirring for 1 hour at the same temperature. After extraction with toluene from the reaction liquid, washing with water and drying were carried out to distill off the solvent. To a 1,2-dimethoxyethane 800 ml solution of the obtained residue and 238 g (0.845 mol) of 1-bromo-4-(trans-4-propylcyclohexyl)benzene, 1160 ml of an aqueous solution of 19.5 g (16.9 mmol) of tetrakistriphenylphosphine palladium and 260 g (2.45 mol) of sodium carbonate was added, followed by stirring for 3 hours under reflux. The mixture was cooled to room temperature, toluene was added thereto for liquid separation, and the obtained organic layer was washed with water and dried, the solvent was distilled off, and recrystallization and purification by silica gel column chromatography were carried out to obtain 240 g of aimed (R)-1-[4-[4-(trans-4-propylcyclohexyl)phenyl]phenyl]-2-pheynylpropane. Melting point: 93.8° C., TSI: 130.8° C., MS m/e: 396 (M+)

1. additionwas dropwise added
2. stirringby stirring for 6 hours
3. temperatureunder reflux
4. temperatureAfter the mixture was cooled to room temperature
5. customThe above reaction liquid
6. additionwas dropwise added to a solution
7. stirringby stirring for 1 hour
8. temperatureThe temperature was raised to 0° C.
9. stirringby stirring for 1 hour at the same temperature
10. extractionAfter extraction with toluene
11. customfrom the reaction liquid
12. washwashing with water
13. customdrying
14. distillationto distill off the solvent
15. stirringby stirring for 3 hours
16. temperatureunder reflux
17. temperatureThe mixture was cooled to room temperature
18. customfor liquid separation
19. washthe obtained organic layer was washed with water
20. customdried
21. distillationthe solvent was distilled off
22. customrecrystallization and purification by silica gel column chromatography
23. customto obtain 240 g of aimed (R)-1-[4-[4-(trans-4-propylcyclohexyl)phenyl]phenyl]-2-pheynylpropane
24. custom130.8° C., MS m/e